Is it a backhanded compliment when someone tells you to try something new because there are others who made it with far less qualifications?

I may be wrong but it reminds me of when my aunt called me an underachiever and I took it to mean that i was being called some type of achiever until I understood the word, which just proved her point. 

Right now, it feels to me like I'm being told to try, not in an encouraging way, but without any concern at all because it doesn't matter what I do and because, "people who are less qualified do and win anyway."